Ethylamine tetrahydrofuran → HCID 67351604, compound

HRID 1672855Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[C:17]2[C:16](=[O:18])[N:15]([C:19]3[CH:20]=[C:21]([C:25]4[O:29][C:28](=[O:30])[N:27]([CH3:31])[N:26]=4)[CH:22]=[CH:23][CH:24]=3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:7]=[C:6](S(C)(=O)=O)[N:5]=1)[CH3:2].[CH2:36]([NH2:38])[CH3:37].C1COCC1>C1COCC1>[CH2:1]([NH:3][C:4]1[C:17]2[C:16](=[O:18])[N:15]([C:19]3[CH:20]=[C:21]([C:25]4[O:29][C:28](=[O:30])[N:27]([CH3:31])[N:26]=4)[CH:22]=[CH:23][CH:24]=3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:7]=[C:6]([NH:38][CH2:36][CH3:37])[N:5]=1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

(S)-5-[3-(7-Ethylamino-9-methanesulfonyl-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-3-methyl-1,3,4-oxadiazol-2(3H)-one (23.6 mg, 0.0472 mmol) obtained in Step 1 was dissolved in THF (2.0 mL), and the mixture was stirred at 90° C. for 30 minutes under microwave (CEM; Discover; 250 watts) irradiation after adding a 2.0 mol/L ethylamine/THF solution (1.0 mL, 2.00 mmol). The mixture was further stirred at 90° C. for 30 minutes under microwave (CEM; Discover; 250 watts) irradiation after adding a 2.0 mol/L ethylamine/THF solution (0.049 mL, 0.0981 mmol). The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (Compound 158) (20.8 mg, 88%).

Workup

stirringThe mixture was further stirred at 90° C. for 30 minutes under microwave (CEM; Discover; 250 watts) irradiation
concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-7e564497de2149d69fc1beed4addf608
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998954B2

Reaction notes

Loading…